jo401428q_si_002.pdf (1.41 MB)

Synthesis of Tetrazole-Derived Organocatalysts via Azido-Ugi Reaction with Cyclic Ketimines

Download (1.41 MB)
journal contribution
posted on 18.02.2016, 20:44 by Olga I. Shmatova, Valentine G. Nenajdenko
A new route to tetrazole-derived cyclic amines based on the TMSN3-modified Ugi reaction with 2-substituted cyclic imines was elaborated. The reaction allows the direct preparation of five-, six-, and seven-membered cyclic amines substituted with a tetrazole ring, which are important types of organocatalysts. The scope and limitations of this method are discussed. In the case of the Ugi reaction with benzyl isocyanide, the N-substituted tetrazoles can be easily debenzylated under catalytic hydrogenation conditions to form NH-tetrazoles in quantitative yields. It was demonstrated that both enantiomers of tetrazole-derived cyclic amines can be prepared by resolution with tartaric acid, thereby initiating a simple route to chiral derivatives. One of the obtained chiral tetrazoles was efficiently used as an organocatalyst in the amination reaction.